Imidazoquines as Antimalarial and Antipneumocystis Agents

Peptidomimetic imidazolidin-4-one derivatives of primaquine (imidazoquines) recently displayed in vitro activity against blood schizonts of a chloroquine-resistant strain of Plasmodium falciparum. Preliminary studies with a subset of such imidazoquines showed them to both block transmission of P. be...

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Published inJournal of medicinal chemistry Vol. 52; no. 23; pp. 7800 - 7807
Main Authors Vale, Nuno, Prudêncio, Miguel, Marques, Catarina A, Collins, Margaret S, Gut, Jiri, Nogueira, Fátima, Matos, Joana, Rosenthal, Philip J, Cushion, Melanie T, do Rosário, Virgílio E, Mota, Maria M, Moreira, Rui, Gomes, Paula
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 10.12.2009
Amer Chemical Soc
Subjects
Animals
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antifungal agents
Antimalarials - blood
Antimalarials - chemical synthesis
Antimalarials - chemistry
Antimalarials - pharmacology
Antiparasitic agents
Biological and medical sciences
Cell Line
Chemical Phenomena
Chemistry, Medicinal
Disease Transmission, Infectious
Drug Stability
Female
Humans
Imidazoles - blood
Imidazoles - chemical synthesis
Imidazoles - chemistry
Imidazoles - pharmacology
Life Sciences & Biomedicine
Liver - parasitology
Medical sciences
Mice
Pharmacology & Pharmacy
Pharmacology. Drug treatments
Plasmodium falciparum - drug effects
Pneumocystis carinii - drug effects
Science & Technology
ANTI-PNEUMOCYSTIS-CARINII
IMIDAZOLIDIN-4-ONE DERIVATIVES
IN-VITRO
TRANSMISSION-BLOCKING ANTIMALARIALS
PLASMODIUM-FALCIPARUM
8-AMINOQUINOLINES
TRAP MASS-SPECTROMETRY
OPPORTUNISTIC INFECTIONS
PNEUMONIA
PRIMAQUINE
Protozoa
Antimalarial
Apicomplexa
Five membered ring
Peptides
Nitrogen heterocycle
Peptidomimetic compound
Quinoline derivatives
Pneumocystis carinii
In vitro
Fungi
Antiprotozoal agent
Plasmodium falciparum
Antifungal agent
Structure activity relation
Bicyclic compound
Dipeptides
Parasiticide
Aromatic compound
Fungi Imperfecti
Chemical synthesis
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Abstract Peptidomimetic imidazolidin-4-one derivatives of primaquine (imidazoquines) recently displayed in vitro activity against blood schizonts of a chloroquine-resistant strain of Plasmodium falciparum. Preliminary studies with a subset of such imidazoquines showed them to both block transmission of P. berghei malaria from mouse to mosquito and be highly stable toward hydrolysis at physiological conditions. This prompted us to have deeper insight into the activity of imidazoquines against both Plasmodia and Pneumocystis carinii, on which primaquine is also active. Full assessment of the in vivo transmission-blocking activity of imidazoquines, in vitro tissue-schizontocidal activity on P. berghei-infected hepatocytes, and in vitro anti-P. carinii activity is now reported. All compounds were active in these biological assays, with generally lower activity than the parent drug. However, imidazoquines’ stability against both oxidative deamination and proteolytic degradation suggest that they will probably have higher oral bioavailability and lower hematotoxicity than primaquine, which might translate into higher therapeutic indexes.
AbstractList Peptidomimetic imidazolidin-4-one derivatives of primaquine (imidazoquines) recently displayed in vitro activity against blood schizonts of a chloroquine-resistant strain of Plasmodium falciparum. Preliminary studies with a subset of such imidazoquines showed them to both block transmission of P. berghei malaria from mouse to mosquito and be highly stable toward hydrolysis at physiological conditions. This prompted us to have deeper insight into the activity of imidazoquines against both Plasmodia and Pneumocystis carinii, on which primaquine is also active. Full assessment of the in vivo transmission-blocking activity of imidazoquines, in vitro tissue-schizontocidal activity on P. berghei-infected hepatocytes, and in vitro anti-P. carinii activity is now reported. All compounds were active in these biological assays, with generally lower activity than the parent drug. However, imidazoquines’ stability against both oxidative deamination and proteolytic degradation suggest that they will probably have higher oral bioavailability and lower hematotoxicity than primaquine, which might translate into higher therapeutic indexes.
Peptidomimetic imidazolidin-4-one derivatives of primaquine (imidazoquines) recently displayed in vitro activity against blood schizonts of a chloroquine-resistant strain of Plasmodium falciparum. Preliminary studies with a subset of such imidazoquines showed them to both block transmission of P. berghei malaria front mouse to mosquito and be highly stable toward hydrolysis at physiological conditions. This prompted Lis to have deeper insight into the activity of imidazoquines against both Plasmodia and Pneumocystis carinii, on which primaquine is also active. Full assessment of the in vivo transmission-blocking activity of imidazoquines, in vitro tissue-schizontocidal activity on P. berghei-infected hepatocytes, and in vitro anti-P. carinii activity is now reported. All compounds were active in these biological assays, with generally lower activity than the parent drug. However, imidazoquines' stability against both oxidative deamination and proteolytic degradation suggest that they will probably have higher oral bioavailability and lower hematotoxicity than primaquine, which might translate into higher therapeutic indexes.
Author Rosenthal, Philip J
Gut, Jiri
Marques, Catarina A
Collins, Margaret S
Mota, Maria M
Vale, Nuno
do Rosário, Virgílio E
Gomes, Paula
Prudêncio, Miguel
Matos, Joana
Nogueira, Fátima
Cushion, Melanie T
Moreira, Rui
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Keywords ANTI-PNEUMOCYSTIS-CARINII
IMIDAZOLIDIN-4-ONE DERIVATIVES
IN-VITRO
TRANSMISSION-BLOCKING ANTIMALARIALS
PLASMODIUM-FALCIPARUM
8-AMINOQUINOLINES
TRAP MASS-SPECTROMETRY
OPPORTUNISTIC INFECTIONS
PNEUMONIA
PRIMAQUINE
Protozoa
Antimalarial
Apicomplexa
Five membered ring
Peptides
Nitrogen heterocycle
Peptidomimetic compound
Quinoline derivatives
Pneumocystis carinii
In vitro
Fungi
Antiprotozoal agent
Plasmodium falciparum
Antifungal agent
Structure activity relation
Bicyclic compound
Dipeptides
Parasiticide
Aromatic compound
Fungi Imperfecti
Chemical synthesis
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Snippet Peptidomimetic imidazolidin-4-one derivatives of primaquine (imidazoquines) recently displayed in vitro activity against blood schizonts of a...
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SubjectTerms Animals
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antifungal agents
Antimalarials - blood
Antimalarials - chemical synthesis
Antimalarials - chemistry
Antimalarials - pharmacology
Antiparasitic agents
Biological and medical sciences
Cell Line
Chemical Phenomena
Chemistry, Medicinal
Disease Transmission, Infectious
Drug Stability
Female
Humans
Imidazoles - blood
Imidazoles - chemical synthesis
Imidazoles - chemistry
Imidazoles - pharmacology
Life Sciences & Biomedicine
Liver - parasitology
Medical sciences
Mice
Pharmacology & Pharmacy
Pharmacology. Drug treatments
Plasmodium falciparum - drug effects
Pneumocystis carinii - drug effects
Science & Technology
Title Imidazoquines as Antimalarial and Antipneumocystis Agents
URI http://dx.doi.org/10.1021/jm900738c
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https://www.ncbi.nlm.nih.gov/pubmed/19799426
https://search.proquest.com/docview/734168006
Volume 52
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